The Tim Ferriss Show Transcripts: Caterina Fake (#360)

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Please enjoy this transcript of my interview with Caterina Fake (@caterina), a long-time Silicon Valley pioneer. Caterina is a co-founder of Yes VC, a pre-seed and seed-stage fund investing in ideas that elevate our collective humanity. Previously, she worked at Founder Collective as a founder partner, served as chair of Etsy, and was a co-founder of Flickr. Caterina sits on the board of Public Goods, the Sundance Institute, and McSweeney’s. She was given the Silicon Valley Visionaries award in 2018 and has received honorary doctorates from both the New School and the Rhode Island School of Design (RISD). She is an early creator of online communities and a long-time advocate of the responsibility of entrepreneurs for the outcomes of their technologies. Caterina is also the host of the new podcast Should This Exist?, which asks, “What is technology doing to our humanity?” Should This Exist? can be listened to on Apple Podcasts, at shouldthisexist.com, or anywhere podcasts are found. Transcripts may contain a few typos—with some episodes lasting 2+ hours, it’s difficult to catch some minor errors. Enjoy!

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, Castbox, or on your favorite podcast platform.

#360: Caterina Fake — Lessons from Flickr, Kickstarter, Etsy, and Much More
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Tim Ferriss: Caterina, welcome to the show.

Caterina Fake: I’m super excited to be here, Tim.

Tim Ferriss: And you’ve been long requested as a guest on the show, and I am really so thrilled to finally have a chance to spend some time together because I feel like it’s been many many years in the making.

Caterina Fake: It has. I remember, actually, when you first moved out to San Francisco, and you and I had some conversation or email exchanged very early on. So indeed.

Tim Ferriss: And I remember I was so impressed with, at one point, one of your responses because I asked if you would, I think, be a panelist or a speaker at some conference. It might have been South by Southwest, could have been another, and you said, “I’m taking a year break from conferences.” And I was so impressed by the categorical decision to not do any speaking engagements that I made a mental note of that.

There’re so many places we could start, but in the process of doing homework for this, I found mentioned, and I wanted to do a fact check on this, of you having plane tickets automatically cancelled, and other issues related to your last name. Is that accurate? Did those things actually happen?

Caterina Fake: This has happened to me many times, in fact. And I discovered that it was actually the systems at KLM and Northwest that would throw my ticket out, my last name being “Fake.” And I have missed flights and have spent way too many hours with customer service trying to fix this problem. Here’s another thing too, is that I was unable for the first two years of Facebook to make an account there also. And probably  all of my relatives.

Tim Ferriss: Do you use a workaround now to prevent these types of problems? Or has it just been resolved at this point?

Caterina Fake: It has been resolved by my not taking those airlines anymore. I’m serious. I actually will see a flight on KLM or Northwest, and will not take it. I’m not even sure if those airlines are around anymore.

Tim Ferriss: I’m not up to speed on the airlines. It’s like, magazines and airlines, which go out of business faster? Despite these travel challenges, you somehow manage to land in Silicon Valley. And we were chatting before we started recording about your, I think the term was “stochastic” path and eclectic background that you have. But could you describe for people how you ended up in Silicon Valley? Did you do Stanford MBA and study computer science before that, and it was the objective all along? How did it come to be?

Caterina Fake: That’s actually not my path, the Stanford MBA. However, what happened was I was living in New York and had spent the summer in Arkansas rock climbing, and was big into rock climbing, and had hooked up with a group of people there, and we were on our way to Nepal to do a big climb.

And so I showed up at my sister’s apartment in San Francisco; she had moved there first. I am from the east coast originally, and I had my ice pick, and my crampons, and my backpack full of gear, and was planning on doing a big climb in the Himalayas. So she, being my older sister, put me up for a couple weeks in her house, and I was visiting her on my way out to Asia. But what happened was my trip was delayed because one of our head climbers had become injured. And then the trip was delayed, and delayed, and then finally it was avalanche season and it was no longer possible for us to do the trek through the Himalayas, and so I ended up staying in my sister’s spare bedroom.

At the time, San Francisco was cheap enough that people had spare bedrooms, and so I just stayed. And my delightful sister, who I love dearly and has always taken care of me throughout my life, her little sister shows up and six months into my stay there, she suggests to me, “Hey, Caterina, you might want to think about getting a job.” So this being 1994, the most interesting thing that was going on at the time in San Francisco was the internet. And so I got started then as a web designer.

Tim Ferriss: And did you have a design background? Let’s flash back six months. So you’re landing in San Francisco en route to this climbing expedition. At that point in time, what did you think you were going to do when you grew up, so to speak? Or over the following five to ten years? Did you have an idea of where you thought you were going prior to the internet entering the picture?

Caterina Fake: Oh, yeah. My background is in art and literature, mostly. And from the age of, I would say, probably about 10 or 11, I had decided that I was going to be an artist and a writer. I was an art school dropout. I graduated from Vassar with a degree in English literature. And I had applied to grad school at Berkeley before this whole internet thing happened, and was planning on getting a PhD in renaissance literature. That was really my true love; I’ve always loved poetry. And the internet, which I’ve always had an interest in, had a computer and had been hacking around with it since I was young, was another alternate path that I took. So I had actually been very interested, and there were a bunch of professors that I went and interviewed with at Berkley. Renaissance literature was my great love.

Tim Ferriss: Do you think that your background, which is in some respects, I suppose atypical for someone who ends up in tech, did you feel that, say, literature has provided you with some type of advantage, or context, or perspective, or other aspects of your background that ended up really assisting you with both operating in the tech world, and investing in the tech world? Do you feel like those things have been in any way an advantage?

Caterina Fake: I really think that people who come from outside of the industry have a superpower that people who have lived within the industry their whole lives, or have spent all of their time in that mindset, it does give you a super power, it does give you an ability outside, to be able to see things in a different way. And if you look at all of the companies that I’ve been involved with, and the investments that I’ve made, they are companies that emphasize creativity, communication, connection, collaboration, and community. And a lot of that comes from this background in humanities that I have.

I really am a big believer in people’s creativity flourishing when they come at things from a different direction and see things in a different way. And in many ways, I’ve always encouraged entrepreneurs, and investors, and people who are interested in entering technology to come at it from a different field, and really emphasize those parts of themselves that are different from the mainstream expectation of who you’re supposed to be, and what you’re supposed to know, and where you’re supposed to go to school. Coming from a different direction is almost always an advantage.

Tim Ferriss: Coming from the interrupted climbing expedition, as you did six months or so after landing in San Francisco, then being encouraged – sounds like very gently and understandingly – by your sister to go consider getting a job, what did the subsequent 12 months or so look like for you when you stepped into that world?

Caterina Fake: This was a very early stage in the internet, and there were no manuals, or guides, or blog posts, or anything like that to help you shape your approach to the industry, and so you had to make it up yourself. It was a very small community of people that were interested in the web at that time, they were all centered down in South Park, which we, at that time, called Multimedia Gulch, which is a funny terminology. It was very early stages. And so I had to teach myself HTML, I had to figure out how to design for the internet. And it was a very experimental, DIY self-education. At the time, getting involved in that at that very early stage, it was such a small community that I just happened to be really lucky that my friend’s roommate, actually, worked at one of the very first web companies and was able to teach me HTML.

Tim Ferriss: And where and when did Flickr enter the scene, or the embryonic stages of Flickr? When did that come onto the radar?

Caterina Fake: It’s interesting because we were actually in the process of building something different when Flickr came about. Everybody calls it pivoting these days, but it was a pivot, and came out of an unsuccessful game. It was also built during the lull after the .com boom, there was the .com bust in 2000, 2001, 2002 was when things were actually looking very bad for technology, and technology businesses, and startups, and the ability to get funding. We were unable to get funding for the game that we were working on, and so Flickr was a kind of Hail Mary that we were able to turn into a very successful business and then lead into the whole web 2.0 era, social media as we know it now. Although when we conceived of it, it was not social media, it was an online community.

Tim Ferriss: And if we look at Flickr as a successful Hail Mary, and we survey the landscape of Hail Marys in the entrepreneurial world, a lot of them don’t work out. A lot of these Hail Marys don’t work out. These sort of death knell, last gasps for breath as funding is running out, often those do not work out, but some do. And there are some examples of these pivots, whether it’s Twitter, or Flickr, or others that did work out. Can you discern what, perhaps, the ingredients were that made it a successful pivot/Hail Mary? Is there a particular way you guys thought about it? Anything at all that you might attribute the success to?

Caterina Fake: You know, it’s funny because there’s a conversation I once had with another investor who said that, “There are some entrepreneurs that are just so bull-headed, and stubborn, and they won’t quit, that companies really go out of business when the founder just quits. When they just stop. When they’re like, ‘I can’t take it anymore.’” And when I was in the Valley, I saw several examples of this. I was dating Ev Williams, the Twitter founder at the time, and it was an amazing thing to see, actually, because Ev had completely run out of cash; it’s the story of startups everywhere: it’s a race against the bank account, really, and he had nothing left when he was starting Blogger, but he just kept on going. It was a miracle. It was amazing to watch.

Blogger was eventually acquired by Google. Google went public, he then had more cash, was able to start the Obvious Corp., which then incubated Twitter. Having seen that first hand, close up, that kind of willful determination, I see that again and again. And when you see things like the pivot that we went through, we were living on cup noodles and not getting paid, and the only guy that was getting paid was the guy who had three kids on our team. Talk about fumes, we were really driving on fumes. And then a miracle happened.

What happened was, we had submitted an application to the Canadian government. Flickr was started in Vancouver Canada, and we had been rejected, actually, for this funding for our startup Game Neverending. And we had apparently checked a little box that said, “Re-submit next year.” Because what happened was, we were truly going out of business. I think we had taken money from our friends and family, and all of that money had been spent. And I remember this, it was December 23rd, it was two days before Christmas, a letter arrived saying, “Congratulations, we are giving you this start-up grant.” And it came out of nowhere. Really, we had a month or two left to pay our front-end engineer, and that was it. So this came out of nowhere, and that was what enabled Flickr to get off the ground.

Tim Ferriss: That’s so wild.

Caterina Fake: Yeah, it was. It was a super scrappy operation. This is days before AWS, and we just didn’t have a lot of cash, and literally the servers were in a colocation center, and we literally had the phone number of the woman who worked down at customs who would call us up and say, “Hey, your new server has arrived from Austin, Texas. Dell has sent you the new server.” We would rush down there, plug in our new server at the colocation center, and load up the software, and keep going. It was a super sketchy foundation on which all of this stuff was built.

Tim Ferriss: There’s certainly some luck involved with the checking of this box, but there were, I would imagine, also some good and probably some bad decisions that were made, but probably some good decisions that were made that in retrospect contributed to what Flickr then became. I was wondering if maybe we could explore one that I have just here under the exploratory bullets, which talks about you and, I think it’s George Oates, spending 24 hours a day, seven days a week, greeting every single person who came to the site. Is that true? Is that something you guys did; manually greeting everyone who came to the site in an effort to build community? Or what was the rationale behind that, if that’s true?

Caterina Fake: Yeah, I think that’s to some degree true. We had, I remember, I looked back in the first three months of Flickr, the team each had posted something like 50 posts a day in the forums on people’s photographs and had really been very strong participants in the community as it was being built. And I really am a big believer in this. I actually wrote an article for Wired at one time talking about how if you read the Bible, Abraham, so and so begat, so and so begat, so and so and it goes on for pages and pages, and I really do believe that the entrepreneur is the Abraham of the company, and so therefore is dictating what the practices are of the community. How everybody behaves; how people respond to other people’s photos.

All of those things I think are basically how communities are built, and staying involved, and being involved, and having that conversation, and being live in that conversation all the time is a really important part of building an online community. And all of this went off the rails a bit when online community was renamed and repackaged as social media. Because then it became a media platform in which people’s attention could be sold, and as we later discovered, people’s data could be harvested, and also sold. And that a very different way of building something than building a community from the ground up, which is, I think, what we were trying to do.

And so I think the community, even now, it’s been acquired by SmugMug, it’s got a new life ahead of it, that’s really the foundation of why it was such a strong community, and how, even after the Yahoo acquisition, and many years later, continued to be a very strong community, and a model of community online.

Tim Ferriss: It also strikes me how many companies that later become viewed as very large, like Airbnb, in the beginning, this also reminds me of this, whether it’s Brian or Joe Gebbia, I know better, talk about the early days of Airbnb, it was highly highly manual. And they would to things that didn’t scale very deliberately until they had to create a system for it. But in the beginning, it was really, really high-touch to build that community in the very early days, and it seems to be something that is sometimes missed by entrepreneurs who start something, and beginning on day one want to scale it to a million users, or 10 million users, or however many million users. Are there any other decisions or behaviors, best practices that you had in those early days that you think were critically important? Or mistakes, either one.

Caterina Fake: Yeah, it’s hard to say. It’s funny because when you look back at something that has been successful, I think there’s a tendency among entrepreneurs to attribute it to some action that they took. And one of the things you mentioned earlier, which I think is actually very important is that we were extraordinarily lucky. We had invented this at exactly the right time. And what had happened was, all of these things were converging at all of the same time. Friendster had come out, had gotten people accustomed to the idea of having a profile of themselves online, and more than half of the households in America had broadband for the first time, more than half of the phones were being shipped with a camera on them. It was just an unstoppable juggernaut because of the time in which it was intended, right? And part of that was being smart, and addressing that market, but a lot of it was also, I think, we were extremely lucky and well positioned to be taken advantage of all of these flows of information.

And Bill Gross, who started Idealab and has been the progenitor of, I don’t know, 500 companies? Many, many companies. He looked at the success of those businesses, many of them succeeded, many of the failed, and tried to figure out what it was about the companies that succeeded that helped them to succeed. And he looked at the team, execution, the financing, the market they were addressing, the timing, all of the things that potentially contribute to a startup’s success, and what he discovered was that more than anything, timing, timing was the thing that made those companies successful. And I think that if this had happened 10 years before to 10 years after, even five years before, or five years after, it wouldn’t have had the same momentum as it does now.

And I look at this as an investor now with Yes VC, my investment firm, and we’re always looking for companies that have timed it just right. That have found a parade and gotten in front of it. That are part of a movement. Because when you have that kind of a movement behind you, there’s some kind of cultural change that’s happening, there’s something that people believe very strongly in, there’s a change that society wants, it makes it so much easier to get ahead. People are more inclined to want the product or the service. They’re more inclined to talk about it. It’s already in a flow that’s moving forward.

Tim Ferriss: How do you, actually maybe we can look at this in a specific example, so let’s take – and this may not be an example of this, but it could be, if we look at Kickstarter. So you were the first investor in Kickstarter, or one of the first?

Caterina Fake: One of the first. And I actually invested in it when it was still a PowerPoint deck. It was not built yet, and Perry, and Yancey, and it was actually brought to me by Sunny Bates, who I think remains on the board now, it was so clear that that had to happen. And it was something that you felt in the culture. Something that you felt around conversations that were happening online. And this was a possibility that needed to bear fruit. It was very clear. And I think a lot of the things, if you look at, for example, Etsy. Etsy was at the forefront of the DIY, handmade movement. It was a rebellion against big-box retail and a return to the marketplace, which has always been a very person to person community-oriented place.

I traveled in Seria and went to those souks, the big marketplaces in Aleppo, which have now been destroyed, tragically. That was one of the most ancient marketplaces in the world. It was like a caravansary, people would bring their camels in medieval times and form a market there, and you could see that that was the genesis of, you talk about the genesis of Airbnb, or Flickr, or all those other companies, the genesis of markets was really sitting down, having a cup of tea, and negotiating for your rug. And Etsy had that, right? Etsy had that. And Kickstarter had that.

And there were these very person-to-person experiences that were manifested in places like Etsy, and Kickstarter, and Flickr, and a lot of these products at the very outset. And I think that that’s another thing that happened at the very beginning of Airbnb, it was very much about people coming together in a very essential and human way. And that was what set those companies on such a strong foundation.

Tim Ferriss: And what did you see that other people didn’t see, or what enabled you to see what you saw that got you to yes with, say, Kickstarter or Etsy, or other examples that might come to mind? Because a lot of these companies that are name brand now faced a lot of rejection and a lot of nos and people didn’t get it. Including people that most folks would consider quite smart. It’s true for Airbnb. Uber was turned down by hundreds of people on AngelList when it went out. What did you see that other people missed? Or did you have – that could be in the companies themselves, or in the founders, or anything else, but what did you see that got you to yes? Because, I’m sorry to interrupt myself and you, because a lot of founders will come in and a very high percentage will claim that they’ve found that parade, right? That they’re in front of these three converging trends that are inevitably going to sweep the world. So how do you end up betting on the right horses?

Caterina Fake: Like we were saying earlier, my difference helps me. I’m also a woman in a male dominated industry. I’m a mom. There’re many things about me that are nontypical. And when I first saw Etsy, it was the beautiful thing, and I actually took it to Reid Hoffman, who had invested in my first company Flickr, and a bunch of other people in the Valley, and they lifted their eyebrows and they said, “Okay, let me get this straight. This is a bunch of women, mostly, knitting sweaters and selling it to each other?” And I said, “Exactly. Don’t you see the opportunity here?” And I think coming from this humanities background where I had spent a lot of time studying culture and society and people, and what was happening around me, and human interactions, and how the culture was changing gave me a special view into that world that was missing, that somehow other people weren’t seeing, that were nontypical, was outside of the pattern recognition of Silicon Valley.

And a lot of the investments that I have made have fallen outside of the typical pattern recognition that everybody takes advantage of in order to spot success. And I think I’ve always had that. My partners at Founder Collective used to tell me this all the time. I would bring in deals, they’d say, “Your deals don’t look like anybody else’s deals. Your deals look very different. The people that you’re backing, the people that you consider as potential entrepreneurs fall far outside of what is typically understood in the Valley as a typical investment.” And they said this to me over and over again, like, “Wow, where did you find these folks?” And most of the time they found me.

And I think part of the reason we started Yes VC, and that we wanted to start a brand new firm, was because we saw that there was a sea change happening in technology, and that people that were nontypical, people that didn’t fit the typical pattern of an entrepreneur as defined by the Valley culture, were now liberated from a lot of prejudices that they’d been working against before. And if there had been an investor in 2004 when I was raising money for Flickr that looked like me, I would have gone straight to her, but there just weren’t that many. And so I think things have changed a lot. And nontypical investors, people from outside of the Valley, people that are in different regions, people of color, women, I think there’s so much more opportunity right now for those kinds of businesses to flourish and are being given a voice. And when all of those companies were starting, it was actually much harder to find people who understood those business models, those founders, and their orientation.

Tim Ferriss: Let’s talk about atypical, and you as an atypical investor for a second because this is part of the reason I was so excited to talk, and I’d love to chat a bit more about a few things you’d mentioned. So you mentioned your familiarity with culture, society, people. And then, whatever it was, five or 10 minutes ago, we talked a little bit about timing. And this is going to be a bit of a long question, so bear with me, was how could someone who wants to cultivate that type of awareness go about developing a better perspective, or a different lens on culture, society, people, and changes that end up getting, in some way, represented by these fantastic opportunities like Kickstarter or Etsy? I’ve read, in doing homework for this interview, that you’ve recommended for entrepreneurs books like The Innovator’s Dilemma. But I’ve also read on your site, caterina.net, a paragraph, I think you’ll recognize this, this is from 2018, but a comment on Stewart Brand’s work, and I’ll just read this because it’s pretty short.

So “Through Stewart Brand’s work, beginning with How Buildings Learn (one of my favorite books) and his work with the Long Now Foundation, I learned to look at time differently, and technology differently, and to think about how time is cooked into everything we do today, especially as regards the ephemeral nature of all the time spent on computers and in online media.”

So I’m curious, if, say, How Buildings Learn, or Stewart Brand’s work, would be something that you would recommend to people coming out of more of the CS, or prototypical Silicon Valley background? If they wanted to develop some of the perspective that you have, are there any resources, or books, or way that you would suggest people explore?

Caterina Fake: I love that you brought this up, Tim, because part of the reason I was super excited to talk to you about this is because I think you and I share an obsession with time.

Tim Ferriss: Yes.

Caterina Fake: And your books are The 4-Hour Workweek, The 4-Hour Body, all of these things having to do with time. Managing your time; thinking about time. And when you really look at it, kind of from the 35,000-foot view, time is all we’ve got. And time management is possibly the thing that I’ve done most in my life in terms of generating the kind of life that I have wanted to lead. And it went way back. Back to when I was young, and I was actually forbidden by the dean at my school from taking any classes before noon because I’m just one of those people, I work really well at night. I’m a night owl, and I could not make it to my classes in the morning. I actually failed a photography class because it was at 8:00 a.m. No way. I couldn’t do it.

And I honestly believe that one of the reasons I’m an entrepreneur, and that I have always worked for myself, is so that I can manage my own time. And I have always thought that the highest standard of living really come from being the master of your own time. Deciding where you want to go in the morning, what you want to do, and that that is so important. And knowing that when you have the energy to put into your work, you can do that. Whether or not it happens at 8:00 a.m. or if it happened at 10:00 p.m. And I actually gave an interview at Businessweek once about my peculiar schedule, in that I wake up in the middle of the night between 2:00 and 5:00 in the morning, and I do three hours of work. I don’t turn on the computer. I write everything on paper; I do my best thinking and writing and ideation during those hours in the middle of the night, and then I go back to sleep and get up and carry on with my day. But without that, that talkative time where I’m uninterrupted, I’m offline. I’m free and liberated in a way that you just don’t get during the work day; it’s a magical time.

Tim Ferriss: I have so many questions. This is great. This is great. So I was going to ask you about this waking up between 2:00 a.m. and 5:00 a.m. I didn’t realize that you went back to sleep. I’ve been reading up, I’ll explain why maybe another time, but on the history of lucid dreaming, and it appears that biphasic sleeping, where people would have a first sleep, wake up and then go back to bed, at various points in history has been quite common. It’s not something that I’ve done a whole lot of. But could you give us an example of what you might work on, on paper in those three hours? So you wake up at some point between 2:00 a.m. and 5:00 a.m. specifically, what do you then do? Is it something that you’ve already planted at the top of a piece of paper as a prompt, and you know you’re going to work on a specific problem? Is it like long-hand stream of consciousness? What do you do during those handful of hours?

Caterina Fake: It really depends. Sometimes I wake up and – I’ve always written books, so I’ve been working on a book now for the past three months, a new book. I write sometimes poetry, I sometimes just open up my journal and start writing. I can be working on a big problem. The five-year plan for my startup or something like that. Any kind of big picture thinking, any kind of thinking that involves creativity, intuition, all of that. The right brain, and not the left brain. And I’ve studied all of these people. I come across these articles, there was an article that was recently sent to me that was about this, I actually forget his name, but he was an AI guru, I think he’s from Cambridge. I did not manage to read the whole article because I got stuck on the very first half where it described how this Cambridge AI genius woke up and he didn’t communicate with anybody until noon. And that he managed to have a relationship with his family and they have developed a language of grunts and smiles, so that his thoughts didn’t get interrupted. And then, when he finally went to work around noon, he had one meeting.

And I was like, “Oh my god, this is a master of time management.” And preserving that flow state in your head, and preserving the ability of yourself to think, and wonder, and ideate is so precious and should be defended ferociously at all costs. And I’ve always felt that way. I’ve always had this – I call it cognitive defense. Really powerful cognitive defense. It’s interesting because this also shows up in some of the investments that we’ve made. For example, one of my theories about cultural movements right now is that there’s this very strong desire to simplify your life. We’re being constantly bombarded with information, with marketing, with new products, and you walk into a grocery store, and you’re confronted with 108 different kinds of toothpaste, right? And like a thousand articles that you could be reading at any given moment of the day.

And one of the investments that we’ve made is this company called Public Goods, which basically give you one shampoo, one conditioner, one dish soap, and sends it to your house so you’re not confronted with all of this paradox of choice, right? Which actually people want to reduce. And people want to constantly reduce the amount of stimulation so that they can focus, and so that they can live a more deep and fulfilled life. And I really think that in our society today, and you depict your podcast and hopefully my podcast, and eliminate all the others. You see what I’m saying? You have to focus in and narrow down and eliminate a lot of the noise in your life as much as possible. It’s a very difficult thing to do. And so I see the time management part of our lives as being just a crucial thing to defend our space, our happiness, and our individual lives.

Tim Ferriss: I was looking at your site earlier today, and found an example of removing noise. And it was a simple example, but might be a jumping off point for exploring other examples. This is DF Tube – that is Distraction Free Tube – which is a plug-in that you use to clean up YouTube. Removes the recommendations on the sidebar, the crap on the homepage, inane commentary, poof. And so I made a note to use that myself. Are there any other tools, or books that you found helpful, or approaches that you believe very strongly in? The waking up in the witching hour and working for a few hours without a screen is, I think, a great example. Then you have the very tactical, like the micro tool, something like this extension. Are there other things that come to mind that you found or find particularly helpful?

Caterina Fake: When I am at my most flourishing and productive self, I’m actually online a lot less. And there’s now all of these tools, Screen Time on Apple, and the Apple phone, and all of these things that I think are great. And during the periods in which I think I’m most flourishing, most productive, what I’m doing is I’m going – I did this for as long as I can, and then I fall out of the practice, occasionally, but I always try to get back is, I would schedule a time to do my email in the morning, 10:30 a.m. to 12:00 p.m. and then again in the evening, 4:30 p.m. to 6:00 p.m. and I would be offline as much as I could in the times in between. Now a lot of us have work that we need to do, and things that we need to do online, but to be super disciplined about the time that you spend online, I think is really important. And I’ve always done this, and I have a notebook that I keep next to my computer and it says WNO on the cover, which stands for When Next Online. And you just write a list, and it says “I need to email my accountant. I need to look up what the name of Bob Dylan’s second album was. I need to go fix this misinformation on this Wikipedia page.” You have the urges during the course of the day to go online, and then the next thing you know, three hours have passed and you’re watching unboxing videos on YouTube, right? And you’re like, “What happened? Where did it go?”

And so I think that you just need to get on top of that. I think that’s one really important thing that you can do. This is kind of a major thing. I fall out of this all the time, you see me watching unboxing videos on YouTube all the time, so you just constantly have to bring yourself back to that and realize how much of a time-suck that is and it can be. And realize also that it’s that kind of activity that’s taking you away from a life fully lived. I remember reading an article on Quora, where somebody said, “I want to be an entrepreneur, as successful as Steve Jobs and Elon Musk. How do I do that?” Right? Many people would like to know the answer to that question.

And one of the respondents was Justine Musk, Elon Musk’s ex-wife. I thought this was wonderful, right? Because she knows firsthand actually what it takes to be Elon Musk, and she responded, “Well, first of all, Elon Musk would never be asking this question in a Quora forum.” And that response stuck with me because it’s true. He was off building PayPal, he was building Tesla, and was off doing that, and not wondering how. You see what I’m saying? He wasn’t reading forums endlessly about that, but was out instantiating those ideas, and that really stuck with me because I think it’s true. You can spend a lot of time in preparation, and I think that’s good to an extent and to a degree, but really living it, really being in it, I think is the most important thing.

Tim Ferriss: Yeah, I always have to reel myself in, in a sense, because I love reading and reading is a very socially acceptable form of procrastinating. So I don’t do it as much online, although I’m certainly guilty of that at times. But Kathy Sierra a long time ago said to me, or it might have been in a presentation she gave, but I was sitting in the audience, about focusing on just in time information, not just in case information, and that really stuck with me because I have a tendency to try and stockpile information in case of the one percent chance that I need A, B, and C in the next six months, but it’s not a great use of time.

Let me ask you about poetry. So you mentioned you sometimes write poetry. And correct me if I’m wrong here, but I have some of your favorite poets including, Wallace Stevens, Shakespeare, Emily Dickinson. Why do you write poetry? What do you get out of writing poetry? What does that do for you?

Caterina Fake: It seems to be an external expression of an internal state. It seems to be the recognition of, and valuing of the inner life. I read something that somebody had written, let me try to figure out who it was…I can’t remember. It was something that I’d read just the other day that was worrying and was very concerned that our modern world made it impossible for people to have an inner life. That the inner life was vanishing from the world. That our life was so much of the time that we would normally spend with ourselves, with our dreams, with our thoughts, was vanishing because it was being filled up constantly with stimulation, entertainment, and our compulsion to be online. And basically, what I see is security exploits of the brain that the internet has managed to insinuate into our lives. And that poetry, writing, dreaming, paying attention to those kinds of things, and the cultivation of an inner life, is something that you have to deliberately do, that you have to protect in your life, and make time for, and recognize as important. And frankly, not do many things.

Many of the opportunities that present themselves, it’s just terrible how much FOMO is created by the internet. It’s endless. And there’s a thousand places that you and I could be right now. And a thousand experiences that we could be having and things that we could be doing. And those of us who are like you, like me, like a lot of the listeners are optimists, we’re possibilists, we’re people who believe in living life to the fullest. And the internet both cultivates that and makes those opportunities available to more and more people, hopefully, and yet too much possibility, as we’ve discovered, shuts us down and deprives us of fully lived experiences.

And so it’s interesting because poetry has always been part of my life. I was a bit of a rebel as a kid and as a student, and I’ve always had a very difficult relationship with institutions. I think my very anti-authoritarian nature is also one of the things that led me to becoming an entrepreneur. And I rebelled against these structures, and one of the very earliest instances of this was in the first grade when all of the other kids were learning to read, and I already knew how to read, and I was basically becoming trouble in the classroom for the teacher because I was impatient and I wanted to read. So I went to the library and I sat and I read poetry with the librarian.

I was only five or six years old, and I still remember some of those poems from when I was a kid. And they were just rhymes. Here’s one I remember [Eletelephony by Laura Elizabeth Richards]:

Once there was an elephant,

Who tried to use the telephant —

No! No! I mean an elephone

Who tried to use the telephone —

(Dear me! I am not certain quite

That even now I’ve got it right.)

Howe’er it was, he got his trunk

Entangled in the telephunk;

The more he tried to get it free,

The louder buzzed the telephee —

(I fear I’d better drop the song

Of elephop and telephong!)

Tim Ferriss: It sounds like a great metaphor for what happens to brains when they encounter the internet for hours a day.

Caterina Fake: Exactly.

Tim Ferriss: How on earth do you remember that? That’s incredible.

Caterina Fake: I have this crazy memory. And I have for a long time, I think, since I was in my early teens, I decided that I would memorize poetry as a way of bringing the beauty of thought and language, and I always felt that poetry was one of the highest achievements of human thought, and beauty, and an embrace of the world. And so I wanted it to be part of me. And so I started memorizing poetry as a way of bringing it into my unconscious. As a way of having it always with me from a very young age, and so I started memorizing poetry as a bit of an eccentric teenager. And I have a lot of that love of poetry, but It’s deep inside. And I can recover a lot of this poetry at times when it’s needed. When you’re going through some kind of crisis or difficult times, or depression, or some kind of bad state you find yourself in. suddenly, some oracle from deep in the unconscious will come out, and Shakespeare will have said exactly the right thing, and you’ll then know what to do. It’s kind of this amazing strategy I’ve carried with me my whole life.

Tim Ferriss: For those people listening who, like me, who have minimal exposure to poetry, or at more point were introduced to the wrong poetry, which was just completely confusing and seemingly designed to remain abstract, and obscure, and confusing, are there any poets or collections you might recommend people start with if they wanted to dip their toe in the water of poetry?

Caterina Fake: I honestly think that there’s no one poet for everybody. And that the best way to start is to just go to, I think it’s poetry.org. It’s this wonderful font of poetry, and just start digging around and find what you love. You mentioned some of the ones that I love. I love Wallace Stevens, I love Emily Dickinson, I love Shakespeare. I wrote my thesis in college on James Merrill. I love W.H. Auden. It just goes on and on. We could talk for hours about this. but it’s important that we do this. I’m going to, Tim, if you don’t mind, dig up this quote from Charles Darwin.

Tim Ferriss: I do not mind.

Caterina Fake: Hang on a second, I’m going to Chrome here and I’m going to say… there is this beautiful thing that he says…I’ll find it, it’s online somewhere.

Tim Ferriss: Yeah, take your time.

Caterina Fake: Okay, I think that this is a beautiful thing because he is an amazing scientist. And he lived the life of the mind. And Darwin’s regret was that he had become, he said, “a machine for grinding out facts a figures.” He had become machine-like in his thinking, and he said, later on in his life, “If I had to live my life over again, I would make it a rule to read some poetry, listen to some music, and see some painting or drawing at least once a week for, perhaps, the part of my brain now atrophied would then have been kept alive through life. The loss of these tastes is the loss of happiness.” And I think that’s pretty powerful coming from as great a scientist as Charles Darwin because we live it, what I call, the technic. We live in a world of mechanistic being and thought and science. And all of those passions that throughout, since time immemorial, has sustained humanity, are getting lost somehow, or they’re slipping away, or they’re not part of our daily life. And I think we have to deliberately put it back in and continually put it back in, and make sure that we don’t lose it.

Tim Ferriss: How much of the poetry that you write for yourself remains just for you, and how much of it do you show to other people?

Caterina Fake: I would say 100 percent of it remains just for me. It’s interesting because many people have asked me this over the years because I’ve actually written half a dozen novels; I have written, probably at this point, two or three books of poetry if it were to be in published form. But I have somehow never let any of that out into the world. And part of it is that it’s such a precious part of me that in some ways, I have a very strong tendency and desire to be successful in the world, and I worry that it will go out into the world and it will be subject to the same laws as have led to my success in business, which it’s a very different thing. And so it’s funny because I find that everyone’s like, “Oh my gosh, this is great, you should publish this,” when it’s encountered. And I’m kind of like, “Well, maybe.” But in the end, it’s so valuable to me, that in some ways, if it were to escape out into the world, it would lose some of its power.

Tim Ferriss: Yeah, I think that’s very wise to protect that. After my first book, I’ve run into a lot of entrepreneurs who talk about, say, taking as a lifestyle business, something they love doing in their spare time, on say, Saturday afternoons. Going surfing, or something like that, and turning it into a business. And I’m always very hesitant to recommend that because if it’s something that is this creative outlet that is pure in a sense, and gives them some reprieve from the expectations and pressure of the outside world, I think it’s very smart to keep that for yourself. And you talked about very deliberately building these things into your life.

And you also mentioned a name, and I might be pronouncing this correctly, but W.H. Auden, am I getting that right? And there’s a quote of Auden’s that I pulled up because I could only remember the first line, but I’d love to talk a little bit about your routines. And the quote goes as follows: “Routine in an intelligent man is a sign of ambition.” Of course, it’s blessed everybody, but, “Routine in an intelligent man is a sign of ambition. A modern stoic knows that the surest way to discipline passion is to discipline time; decide what you want or ought to do during the day, then always do it at exactly the same moment every day, and passion will give you no trouble.”

Okay. I’ve read that you very often will eat the same entrée at certain restaurants if you decide you like something. Are there routines that are particularly important to you aside from those that we’ve already discussed? Anything that you make sure you do in the mornings, or that you make sure you do in winding down, or that you do once a month, once a week, once a quarter? Are there any particular routines that help you in structuring your life and your time that you can think of?

Caterina Fake: I have a very idiosyncratic schedule. And the reason for that is that I have, like you say, I find that thing in the restaurant that I love, and I always order it. Because it’s been proven again and again that the burden of decision-making wears you down. And that the fewer decisions that you make over the course of the day, the better decisions that you can make, and the more energy that you have left over for the important decisions in your life. And so famously, Albert Einstein had one suit of which he had five different versions, or something like this, so he didn’t have to think about what he’s going to wear in the morning. Eat the same food. I kind of feel as if these patterns – if you figure out what it is that you’re happy no longer making the decisions about. It’s one of the principles behind Public Goods, this company that I mentioned earlier, is that you don’t have to think about what shampoo to buy. You just don’t have to think about it anymore. You kind of check that box, it’s done, you’ve got a default.

And so building these defaults into your life is super important. Things that you don’t want to think about anymore. And whether that be what you eat, what you wear, things that you’re less invested in. So that, when you’re in like my witching hour, or the hour of the wolf, or whatever you call that, when I’m in that state, I can go wide, right? I can make a thousand decisions. I have freedom to go into dark corners that I haven’t yet explored that I can think really broadly in, be more creative, and have dreams and revelations that are just not possible if you’re crowded into tiny decisions all the time.

Tim Ferriss: Let me take a step back. So you mentioned in passing something when we were discussing poetry, and how certain poems or phrases would come to mind at seemingly the perfect moment when you need it the most. And you mentioned depression very briefly, and that’s certainly something that I have some personal experience with; is that something that you also have personal experience with?

Caterina Fake: Yeah. When I was a teenager, I was actually quite a depressed teenager. I went through a super bad period of my life when I was in that state that’s familiar to a lot of depressed people where I just couldn’t get out of bed in the morning, and just wanted to stay there all day, and was reluctant to expose myself to the world because I felt very vulnerable and needed to basically hide in my cave. And I think that many of us go through these. It’s just common to the human experience that this be a state. And I honestly think there’s a reason for it, right? I dislike like the term depression, because I think a lot of it is better described as melancholy, or despair, or there are older words that seem to describe it. It seems so clinical to talk about it in terms of depression, because I think that it’s part of a fully lived life to go through these periods of deep unhappiness, and dissatisfaction, and questioning, and despair, even.

And without that, you live always on the sunny side of life, I talk about this in the Jungian sense of the shadow. If you’re constantly rejecting the shadow, if you’re constantly living life on the sunny side – this is what happens on social media, and this is why social media can be so diminishing of people’s humanity is that people are always, I call it social peacocking, right? They’re showing how great their life is. They’re showing all of their happy moments. They’re showing all of their successes and not their failures. All other triumphs, and not their doubts. And basically, providing a highlights reel of their life, and this is very damaging to the psyche, to people’s humanity of not acknowledging, living, and frankly, giving time and space to those parts of yourself that are less savory. That are mistakes. I see it all around. And you see it all around, right? You look a all of your happy, successful friends on Facebook, or Instagram, or what have you, they’re always going fabulous places and doing fabulous things. But what about the shadow, right? What about the shadow?

There’s this really wonderful essay that I encourage everybody to read by the science fiction writer Ursula Le Guin, about the shadow. I talk about it, there’s a blog post on my website that’s called Social Peacocking and the Shadow. And in it I link to a short story by Ursula Le Guin about the shadow, which I think is a very important part of people’s humanity, which somehow is not being given space online.

Tim Ferriss: I’ve not yet read the piece, but how would you suggest, you can either suggest or talk about your personal experience, people accept the shadow, or work with it without falling into a dangerously deeper extended state of despair?

Caterina Fake: Like a pit of despair?

Tim Ferriss: Yeah, exactly.

Caterina Fake: Well, it’s interesting because I actually think that the way to start out with that is to accept the shadow in other people. Because we have this idea of other people as being more rich, successful, beautiful, happy, they’re in a better relationship, they have better teeth, they have thicker hair, I don’t know what the thing is, right? Some insecurity that we have we see in others as something that we don’t have. And there’s a wonderful sonnet by Shakespeare on the subject. I think it’s sonnet…what is it? Hang on a second…

Tim Ferriss: Take your time.

Caterina Fake: Sonnet Shakespeare, which one is it? That’s what I mean about the poems that come back. I think it’s 29. Sonnet 29, yes. Here it is. Can I give you this poem?

Tim Ferriss: Yes, please.

Caterina Fake: Okay. It’s Sonnet 29 by Shakespeare.

When, in disgrace with fortune and men’s eyes,

I all alone beweep my outcast state,

And trouble deaf heaven with my bootless cries,

And look upon myself and curse my fate,

Wishing me like to one more rich in hope,

Featured like him, like him with friends possessed,

Desiring this man’s art and that man’s scope,

With what I most enjoy contented least;

Yet in these thoughts myself almost despising,

Haply I think on thee, and then my state,

(Like to the lark at break of day arising

From sullen earth) sings hymns at heaven’s gate;

For thy sweet love remembered such wealth brings

That then I scorn to change my state with kings.

Tim Ferriss: Beautiful.

Caterina Fake: It’s a beautiful poem, and I think what it speaks to is the envy, you know, “Wishing me like to one more rich in hope.” “Featured like him, like him with friends possessed,” and you see it all around you, especially when you’re in the state of despair. And it seems as if the world all around you is full of delight, and success, and happiness that is somehow unavailable to you. But what this poem does is it – “Haply I think on thee.” Right? And often this is ready as a loved poem as a celebration of the relationship that Shakespeare is presumably in when he’s writing all of these sonnets, but when you really think about it…

Mr. Rogers famously says, “Think about all of the people that loved you into being.” Right? Those people are not necessarily your lover, but they’re your mother, they’re your sister, there’s that teacher that saw something in you that other people didn’t see. It’s your friend. And it’s all around you. All you have to do is stop looking at those people that have the things that you wished you had, and look at those people that saw that in you, and realize that they’re all around you. So that’s what that poem does to me. And I feel as if, if you have all of these poems deep inside you, that they will come to you when you need them.

Tim Ferriss: You’re making me think a bit, I hadn’t thought about it in those terms, but only in the last few years I’ve started reading some very easy to read, very easily digested poetry by people like Hafez, and a lot of Sufi poetry.

Caterina Fake: Rumi?

Tim Ferriss: Yeah, Rumi as well. And they do stick. They really do stick. And they seem to have a particular stickiness. A greater stickiness than, perhaps, more clinical nonfiction. Something that is really artfully woven into beautiful language just has a higher stickiness factor because these poems do come to mind at the right time. Just never thought of it quite the way that you’re presenting it.

Have you found anything else useful for embracing the shadow, but not falling into a pit of despair? Or if you’ve run into entrepreneurs who are going through a pit of despair, which is certainly not uncommon. Are there any particular recommendations that you’ve made or would be prone to make?

Caterina Fake: Well, I think that when people are depressed, they’re also in some ways ashamed of it. And I think that’s one of the things that makes it feel so isolating, is that we feel that other people will judge us. That bad things could happen as a result of our revealing these parts of our self that are so troubled, or despairing, or unhappy, or failing, or unsuccessful. And that we always feel as if we’ve got to present our best face to the world. And this can be one of the things that makes it impossible to get out of it. And so one of the things that’s most important, especially in our world of diminished relationships with others is to constantly be in communication with others, to know who our friends are. To revive those lost friendships that we’ve had in the past that are very meaningful to us. To resume our closeness to others, and frankly, as Rumi would say in one of his beautiful poems, “Cry out in your weakness.” Of course, there’s a poem for everything. But this one is: “Cry out in your weakness because there are helpers in the world who will rush to save anyone who cries out. Like mercy itself, they run towards the screaming and cannot be bought off.” And if you address your suffering to others, you find that the suffering is universal. That we all go through these moments of shame, indignity, depression, unhappiness, failure. And that anybody who’s pretending that they don’t is just not true.

Crying out loud and weeping, Rumi says, are great resources. Right? Give your weakness to one who helps. It’s a beautiful poem. I think if you search for it, it’s called Cry Out in Your Weakness. And that is a very meaningful poem, I think, for people who are suffering because it’s basically giving you permission, which I think a lot of people need, to cry out in your weakness.

Tim Ferriss: Yeah. I really appreciate you being willing to talk about this and explore it a bit because it is a constant, like you said, and it’s come up so many time sin these podcasts, whether it’s with these brutal stories of rejection that Brandon Stanton of Humans of New York is telling, or any number of hundreds of examples that have come up. Like you said, it’s an illusion, and a really crippling illusion when you’re not only depressed, but are ashamed of it, feeling like you’re somehow uniquely flawed because that’s just not the case. So I appreciate you being willing to chat about this. and maybe we can continue on the shadow side for just a few more minutes and then we’ll shift gears.

You have an incredible memory; you have an incredible track record. I think a lot of the people listening, or some people, would certainly find that intimidating, which is part of the reason why also I wanted to bring up the depression just to humanize the profile a bit. Are there any failures, we’ve talked a lot about successes and known names, but are there any failures or apparent failures of yours that have set you up in some way for later success? Any noteworthy failures that come to mind? And if you don’t like the word failure, you can use something else.

Caterina Fake: It’s perpetual. It’s hard to single out a single failure. You look back at your miseries, your failures, the companies that didn’t succeed, the relationships that didn’t succeed, the great hope that you had for this or for that, and realize that you spent years and years working toward some failed project, or relationship that didn’t work out, or some kind of track that you fell into and it was a struggle to free yourself. It’s funny because I think that my orientation as a perpetual optimist leaves me with a sense of forward motion from all of those things.

One of the things that we talked about was how when I was a teenager I went through a very deep depression, and a state of despair and melancholy, to use different terminology around it. And I think always those periods were very formative. They are very important. You go back to them and those moments when you’re at your worst, at your weakest, at your least successful, and most alone, and look back at the path that you took out of them, and the ability to emerge from them, and to keep going in spite of them are some of the most meaningful parts of your life. Is that you have, really, reached the depths of despair, and have recovered from them. And the importance that that gives you, going forward, and your strength comes from that. And if you’re never tested, and you’re never in that kind of situation, God help you. It’s not a good state, right? The fullness of your humanity is emerging from those depths.

I’ve always felt that. And without that, without that experience when I was a teenager, without some of those experiences from my childhood, without those experiences perpetually throughout life, life cycles through highs and lows like that, and to appreciate those periods and not struggle to ignore them or somehow eliminate them from your life, is, I think, one of the healthiest things that you can do.

Tim Ferriss: And from people listening who are willing to have that broad spectrum of experience, including the dark moments, but are listening with envy to your talk of optimism, are there any books – I know this is the type of question that won’t die from me, but are there any tools, habits, books, anything that you would recommend to people who want to cultivate a more constant optimism? If they might have been just beaten into cynicism by spending too much time on the internet or whatever it might be, what would you recommend to those people?

Caterina Fake: Honestly, I think that a great deal of emphasis on long form reading, I think you and I both embrace this, and love books and love reading, and I know you read philosophy and Seneca, and I read Jung and poetry, go long-form, not short-form. Go deep, right? And not broad. I think that this is actually a really important thing. There’re a dozen books, and I can even write a list of these and you can post it in the podcast.

Tim Ferriss: In the show notes.

Caterina Fake: In the show notes, exactly. I can write you, oh my gosh, a list of a dozen or more books that have helped me throughout my life.

Tim Ferriss: Oh, for sure. 100 percent yes and yes. If you can mention any of them now, you don’t have to mention all of them, but all of them that come to mind right now, that was going to be the next place I went, so…

Caterina Fake: Yes. Good. So let’s just start. Part of the reason that I’m actually on the internet and love the internet so much is because of Jorge Luis Borges, who I’m a huge fan of, and actually was the motivation for me going online because I had discovered a community of Borges fanatics in Denmark that I communicated with very early on in my internet career. So that’s a big one. I think the best book of his to start with is Labyrinths. And it’s so much about the internet. It’s kind of the internet before the internet. It’s a beautiful thing. As I mentioned, poetry has been a huge part of my life, I love all of the ones mentioned previously: W.H. Auden, Wallace Stevens, Emily Dickinson, Paul Celan, Shakespeare, of course, and contemporary poets. There are wonderful poets out there that I look forward to their work. Natalie Shapero, Brenda Shaughnessy, the list goes on. I can put together a list for you of poets that I love and respect. I love, also, the ones you were talking about: Hafiz, Rumi, Kahlil Gibran; there’s a lot of really wonderful poets from the east that I think bear attention from us.

Tim Ferriss: Are there any other, whether it’s fiction or nonfiction long reads that you would recommend? And for people listening, I’ll definitely put all these in the show notes, so you’ll be able to access all these, but if any other come to mind. Jorge Luis Borges is just incredible in terms of the wordsmithing, and the art of his prose is really staggering. So I definitely second that.

Caterina Fake: I use Goodreads. And goodreads.com is actually a really great place for people looking to discover new books. It’s actually now owned by Amazon, and I put all of the books that I read there because I read a lot. I read at least a book a week. And I’m re-reading, currently, The Odyssey by Homer in a new translation by Emily Wilson. Other books that I have found to be really great that I’ve read in the past year are — a really wonderful book, A Tomb for Boris Davidovich by Danilo Kis; Hannah Versus the Tree by Leland de la Durantaye; Ethan Frome by Edith Wharton. I’m honestly just going through this because I have this massive list. The White Goddess, which is a very meaningful book by Robert Graves, which is about poetry and its sources. I’ve reread The Upanishads. There’s the writer who I just adore, W.G. Sebald, I don’t know if you’re familiar with him.

Tim Ferriss: I’m not.

Caterina Fake: But The Emigrants by him is just an amazing book. I could go on and on.

Tim Ferriss: What books, they could be from that list or otherwise, have you gifted the most to other people, if you gift books?

Caterina Fake: There’s a couple of wonderful books that are actually illustrated books that I have given out to many people, and I think it’s unfortunately out of print. There’s one called Drawings and Observations by the artist Louise Bourgeois, which is fantastic, and I’ve given that to so many people, as well as The Principles of Uncertainty by Maira Kalman. She’s famously an illustrator. Really beautiful books and full of life-giving thoughts. And you can tell that these women have lived very rich, profound lives, very thoughtful lives, very meaningful lives, and it’s there in the books. There’s another really wonderful book that I’ve also given out to a lot of people called Letters of Note. And that is letters that have been collected throughout the ages.

Tim Ferriss: I’ve been meaning to grab that compendium, so I’m really glad that you just mentioned that, Letters of Note. Check and check. To add to my ever-growing reading list. So you were just mentioning rich lives. We were discussing, or you were mentioning earlier the paradox of choice that many of us face, and certainly, you have more opportunities than you could possibly ever take advantage of in subtotal. Why decide to do a podcast? What was the catalyst or the reasoning behind that? Why Should This Exist? You have finite time, why apply it to that?

Caterina Fake: Well, I think that there’s a super important conversation going on in technology going on right now in the culture in which we live, that needs to be had. I was on my friend Reid Hoffman’s podcast, Masters of Scale, and I loved that experience. I love podcasts just in general, but this one was very gratifying for me because I had done what I thought of as a fairly garden-variety interview with Reid, and they had turned it into a story with conflict, and suspense, and drama, and made it super interesting. I loved it. I loved the podcast, I thought, these producers are geniuses, and June Cohen of Wait What, who produces Masters of Scale started a conversation about this new podcast and realized that the next conversation to be had in technology was about the human consequences of the technology that we’ve been building.

And I think that there has been, going back to the theme of the sun and the shadow, has been all about the sun. And we’re suddenly realizing that the shadow, which is always there, has now emerged. And we’ve seen what damage technology can potentially do to our humanity. And it was time for this podcast to come into being. So it just seemed as if, in some ways, this podcast is inevitable. It seems as if this is a conversation that’s happening now that needs to be emphasized and can potentially build a future that we’re deliberately building, and not lead us into unintended consequences that we’ve seen happen over and over again, most recently in the story of technology.

Tim Ferriss: Can you describe one of the episodes that comes to mind? Whoever is featured, what does the structure of a sample episode look like? What type of technologies, or topics, or entrepreneurs are you discussing?

Caterina Fake: So what we do is we find an entrepreneur who’s building a new interesting technology. And some of the interesting things have to do with AI, or CRISPR, or gene editing, and neuroscientific supplements to help us learn faster. Technologies which are in development where there’re entrepreneurs who are actually building it currently. And we have those conversations, and we bring in people from the industry, from outside the industry, people who have different ideas, psychologists, sociologists, historians, perhaps, and people who have a different perspective on technology and how it might impact our humanity. And then we have a conversation workshop with the entrepreneur about the potential outcomes, utopian or dystopian, of this technology, and how to steer it towards its best possible future.

That is really the best format of the show. And I think that this conversation, hopefully, will become part of the dialog about how companies are built — how they’re thought about — and how, at the very beginning of building these technologies are, frankly, carried out throughout the process of building these technologies that we not only ask the question: can this exist? Because so much of technology has made it possible for so many things to exist, but should this exist?

Tim Ferriss: Do you think there are safeguards or externally enforced constraints, or regulations of any type that could or should steer technology development and company formation? Or are we dependent on the internal ethics and moral compasses of the people who are developing these companies? Certainly, it’s a false dichotomy, you could have both, but I’m curious how you think about that.

Caterina Fake: I do think that we have, in Silicon Valley, enjoyed incredible latitude, and have been, basically, assuming that we have the ability to self-regulate. I don’t think that anybody starts off with this idea of being the supervillain, right? I don’t think anybody starts off in, “Haha, I’m kind of a Bond villain in my hideaway. I’m going to bring about the destruction of the earth!” Nobody starts out that way. I think that we all start out with best intentions and as Baudelaire has said in one of his many beautiful poems, we descend to hell by short steps, and we end up loving what we hate, and hating what we love. We end up doing things that we don’t intend.

And the constant questioning, the constant vigilance, the practice of asking ourselves the question, “Should this exist? Who is this harming? How do I remove bias from my AI? How do I make sure that this doesn’t fall into the hand of the wrong people? How is it that I continually think about the outcomes of my technology and its effect on people and what it might do to them and their behavior, and constantly having that as part of the process of building something new is a very important part of putting it on its right track and building the kind of future that everybody had hoped to build from the outset?”

Tim Ferriss: Well, I am very much looking forward to hearing these episodes, and also seeing how the conversations develop over time, right? I think it’s an important conversation and an increasingly important set of questions, and maybe just lens through which to look at building. And I’m particularly interested in your CRISPR episode. Could you describe for a moment, for people who don’t recognize the term, what CRISPR is, or what it represents?

Caterina Fake: Well CRISPR is, in short, it’s gene editing. It’s the ability to change people’s genes, DNA. And this has incredible possibility and Frankenstein-like potential. I think that people have become very alert to and alarmed by the possibilities, the unintended consequences of introducing edited people, edited animals, edited any form of life, really.

Tim Ferriss: Yeah, virus, bacteria, you name it.

Caterina Fake: You name it, viruses, bacteria. Introducing, basically, the human touch into it. Assuming what, in prior eras and in current eras are actually thought of as the hand of God. And putting that in human hands. And this kind of Promethean impulse that people have to seize the power. Prometheus famously using the power of fire from the gods and wreaking untold destruction upon the earth. There’re just constant warnings throughout historical literature, and Greek mythology, and biblical literature, and modern-day nonfiction, about what happens when we enter the anti-pristine, we enter the era of humankind manipulating the world in a way that is potentially leading us to conflagration and the end. And some say the world will end in fire, some say in ice, right? This is the wonderful poem by Robert Frost. We will somehow bring about our own destruction. And because of our incredible power and ability, I think that we should take responsibility for having that power. And Stewart Brand, who you mentioned earlier, he was one of the progenitors of the Whole Earth Catalog, and in it he said that we are as gods and might as well get good at it.

Tim Ferriss: I have a copy of the updated last Whole Earth Catalog, which was given to me as a Christmas present by my mom about 10 feet from my right side right now. It’s an incredible book and a very good statement on Brand’s part. It’s mind boggling to think about the promise and perils of many of these technologies.

Caterina Fake: Right. Stewart Brand is now working on bringing extinct lifeforms back to life. bringing back the saber-tooth tiger, and the woolly mammoth, amazingly. And that kind of awakened possibility, and dreams, and excitement in the sense of, wow, wonder, the wonder of technology, the wonder of science, right? And then also, terror and fear.

Tim Ferriss: Exciting and scary time to be alive. So I look forward to listening to you explore it with these various entrepreneurs and commentators. Let me ask one more question. It’s sometimes one that’s tough to answer, but I’ll ask it and then we’ll wrap up in just the next few minutes. But the question is one I like to ask, and that is if you could have gigantic billboard, metaphorically speaking, anywhere with anything on it, it could be a quote, it could be a word, it could be a question, anything noncommercial, but in the interest of getting a message of some type out to, say, billions of people, what might you put on that billboard?

Caterina Fake: It’s funny. I think of the basic truths as being a fairly straightforward, frankly boring statement, right? You should brush your teeth regularly; you should not let the grass grow on the path to your friend’s door; you should be kind to one another — they should like platitudes when you say them, when you see them on billboards, and yet they are profoundly true. So frankly, nothing exciting. Mainly, be kind.  

Tim Ferriss: Yeah. Yeah, I think it’s two very important words, and I think that your capacity for being kind may be inversely proportionate to the amount of time you spend on the internet getting poked in the brain by really short form drivel that is weaponized and commercialized, which comes back to the long-form recommendations, and the poetry, and all the other things. I really enjoy having a chance to chat with you like this, in long-form. And I thank you for taking the time to have the conversation. So thank you very much.

Caterina Fake: Yeah. No, this has been a great conversation. Thank you so much for inviting me.

Tim Ferriss: And people can find you on Twitter @caterina, find the podcast, shouldthisexist.com, or on Apple podcasts, and anywhere else podcasts might be found. Caterina.net is where they can find your writing including the Social Peacocking and the Shadow, and the other posts that have come up in this episode for people listening, of course, I’ll add links to everything, including the books that Caterina, I would love for you to send me, and I’ll put them in the show notes. I’ll put those at tim.blog/podcast, and you can just search Caterina or Fake, it will pop right up. Is there anything else you’d like to say? Any parting comments, things you’d like to suggest of people listening, anything you’d like to ask of them, anything at all you’d like to mention before we wrap up?

Caterina Fake: Well, I think that the biggest thing I’ve been working on recently has been the Should This Exist? Podcast, so listen, respond, subscribe, that’s a big thing, and engage in that conversation.

Tim Ferriss: Great. Well, we’ll send plenty of people in that direction. And once again, I really appreciate you making the time to have this conversation. I’ve really really enjoyed it. So hopefully, we’ll have a chance to break bread, or have coffee in person at some point, and I really look forward to listening to the show. So thank you again for that. And to everybody listening, be kind. Be kind. Experiment, go deep, not necessarily wider, and check out some of the books that I’m gonna put into the show notes that Caterina has recommended. And until next time, thank you for listening.

Posted on: February 21, 2019.

Please check out Tribe of Mentors, my newest book, which shares short, tactical life advice from 100+ world-class performers. Many of the world's most famous entrepreneurs, athletes, investors, poker players, and artists are part of the book. The tips and strategies in Tribe of Mentors have already changed my life, and I hope the same for you. Click here for a sample chapter and full details. Roughly 90% of the guests have never appeared on my podcast.

Who was interviewed? Here's a very partial list: tech icons (founders of Facebook, Twitter, LinkedIn, Craigslist, Pinterest, Spotify, Salesforce, Dropbox, and more), Jimmy Fallon, Arianna Huffington, Brandon Stanton (Humans of New York), Lord Rabbi Jonathan Sacks, Ayaan Hirsi Ali, Ben Stiller, Maurice Ashley (first African-American Grandmaster of chess), Brené Brown (researcher and bestselling author), Rick Rubin (legendary music producer), Temple Grandin (animal behavior expert and autism activist), Franklin Leonard (The Black List), Dara Torres (12-time Olympic medalist in swimming), David Lynch (director), Kelly Slater (surfing legend), Bozoma Saint John (Beats/Apple/Uber), Lewis Cantley (famed cancer researcher), Maria Sharapova, Chris Anderson (curator of TED), Terry Crews, Greg Norman (golf icon), Vitalik Buterin (creator of Ethereum), and nearly 100 more. Check it all out by clicking here.

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